Hydrochloric Acid → HCID 86594151, compound

HRID 2223005Notes

Reaction equation

HRID 2223005 reaction equation
[O:1]=[C:2]([OH:11])[CH2:3][N:4]([CH2:8][CH2:9][OH:10])[CH2:5][CH2:6][OH:7].[C:12]([OH:35])(=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[C:36](Cl)(=[O:40])[C:37](Cl)=O.Cl.[Cl-].[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:36]([O:10][CH2:9][CH2:8][N:4]([CH2:3][C:2]([OH:11])=[O:1])[CH2:5][CH2:6][O:7][C:12](=[O:35])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=[O:40])[CH2:37][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8215Docosanoic AcidHCID 8761BicineHCID 65578Oxalyl chloride

Product 1

HCID 86594151HCID 86594151, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

Bicine (0.95 g, 5.82×10−3 mol, Aldrich®, 99+%) was added to chloroform (30 mL, anhydrous, Aldrich®, 99+%). A concentrate of docosanoyl chloride, prepared by the reaction of docosanoic acid (4.12 g, 1.14×10−2 mol, Aldrich®) with excess oxalyl chloride (Sigma) in chloroform, was added dropwise to the suspension. After stirring for a few minutes, excess pyridine (1.5 mL, anhydrous, Aldrich®, 99+%) was added to the flask. The flask was refluxed overnight. The reaction mixture was acidified with dilute HCl saturated with sodium chloride (Mallinckrodt, AR®). The aqueous phase was separated. Any remaining volatiles were removed from the organic phase under reduced pressure with mild heating. The glassy product was recrystallized from ethanol (Mallinckrodt, AR®). The product was recovered by filtration as an amorphous white solid. The product weighed 2.86 g after vacuum drying for a 61% yield; mp 73-75° C.; Rf=0.23 (silica gel, 10:1; chloroform-methanol). 1H NMR (CDCl3, 99.8% D, 1% TMS, Aldrich): 0.880 ppm (t,); 1.254 ppm (s); IR (paraffin oil) OH 3,100 cm−1; CO 1,760 and 1,700 cm−1 C—O 1,180 cm−1.

Workup

  1. concentrationA concentrate of docosanoyl chloride
  2. additionwas added dropwise to the suspension
  3. temperatureThe flask was refluxed overnight
  4. customThe aqueous phase was separated
  5. customAny remaining volatiles were removed from the organic phase under reduced pressure with mild heating
  6. customThe glassy product was recrystallized from ethanol (Mallinckrodt, AR®)
  7. filtrationThe product was recovered by filtration as an amorphous white solid
  8. customdrying for a 61% yield

Sources & evidence

ORD record
ord-f394339a6d484f6fbfe4256fd1653d4b
Source dataset
uspto-grants-2008_05
Patent number
US07374745B2

Reaction notes

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